# US 4,398,943 A · Triazolinone derivative and herbicidal use thereof

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- Number: US 4,398,943 A
- Document ID: US4398943A
- Status: Granted
- Kind: A
- Application number: 06/331,064
- Filed: 1981-12-15
- Granted: 1983-08-16
- Earliest claimed: 1980-12-25
- Assignees: Nikon Nohyaku Co., Ltd.
- Inventors: Mitsuru Kajioka; Katsumasa Okawa; Kuniaki Taninaka
- Web page: https://patentgrep.com/patent/US4398943A

## CPC

- A01N 43/653: 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- A01N 47/02: the carbon atom having no bond to a nitrogen atom
- C07D 249/12: Oxygen or sulfur atoms
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

There is provided a new herbicidal compound of the formula, ##STR1## wherein R.sup.1 is an alkyl group; R.sup.2 is an alkynyl group, a halomethyl group, or a haloethyl group; and X is an alkoxy group, an alkenyloxy group, an alkoxy-alkoxy group, an alkynyloxy group, a hydroxy group, a halomethyloxy group, or a haloethyloxy group.

## Claims

### Claim 1

A .DELTA..sup.2 -1,2,4-triazoline-5-one derivative represented by the formula (I) ##STR24## wherein R.sup.1 is a C.sub.1 -C.sub.4 alkyl group; R.sup.2 is a C.sub.3 -C.sub.5 alkynyl group, a halomethyl group, or a haloethyl group; and X is a C.sub.1 -C.sub.4 alkoxy group, a C.sub.2 -C.sub.6 alkenyloxy group, a C.sub.2 -C.sub.6 alkoxyalkoxy group, a C.sub.3 -C.sub.8 alkynyloxy group, a hydroxy group, a halomethyloxy group, a 3-chloro-2-propenoxy group, a 1-ethynyl-1-cyclohexyloxy group, or a halethyloxy group.

### Claim 2 (depends on 1)

A .DELTA..sup.2 -1,2,4-triazolin-5-one derivative of claim 1, wherein R.sup.2 is the halomethyl group.

### Claim 3 (depends on 2)

A .DELTA..sup.2 -1,2,4-triazolin-5-one derivative of claim 2, wherein the halomethyl group is a difluoromethyl group.

### Claim 4 (depends on 1)

A .DELTA..sup.2 -1,2,4-triazolin-5-one derivative of claim 1, wherein X is a C.sub.1 -C.sub.4 alkoxy group, a C.sub.2 -C.sub.6 alkenyloxy group, a C.sub.2 -C.sub.6 alkoxyalkoxy group, a 3-chloro-2-propenoxy group, a 1-ethynyl-1-cyclohexyloxy group, or a C.sub.3 -C.sub.8 alkynyloxy group.

### Claim 5 (depends on 1)

A .DELTA..sup.2 -1,2,4-triazolin-5-one derivative of claim 1, wherein R.sup.2 is a halomethyl group; and X is a C.sub.1 -C.sub.4 alkoxy group, a C.sub.2 -C.sub.6 alkenyloxy group, a 3-chloro-2-propenoxy group, a 1-ethynyl-1-cyclohexyloxy group, a C.sub.2 -C.sub.6 alkoxyalkoxy group, or a C.sub.3 -C.sub.8 alkynyloxy group.

### Claim 6 (depends on 5)

A .DELTA..sup.2 -1,2,4-triazolin-5-one derivative of claim 5, wherein the halomethyl group is a diflouromethyl group.

### Claim 7

1(2,4-dichloro-5-isopropoxyphenyl)-3-methyl-4 -difluromethyl-.DELTA..sup.2 -1,2,4-triazolin-5one.

### Claim 8

1-(2,4-dichloro-5-allyloxyphenyl)-3-methyl-4-difluromethyl-.DELTA..sup.2 -1,2,4-triazolin-5-one.

### Claim 9

1-(2,4-dichloro-5-pro pargyloxyphenyl)-3-methyl-4-difluromethyl-.DELTA..sup.2 -1,2,4-triazolin-5-one.

### Claim 10

1-(2,4-dichloro-5-me thoxymethoxyphenyl)-3-methyl-4-difluoromethyl-.DELTA..sup.2 -1,2,4-triazolin-5-one.

### Claim 11

A herbicidal composition comprising an effective amount of a .DELTA..sup.2 -1,2,4-triazolin-5-one derivative and a diluent, said derivative being represented by the formula ##STR25## wherein R.sup.1 is a C.sub.1 -C.sub.4 alkyl group; R.sup.2 is a C.sub.3 -C.sub.5 alkynyl group, a halomethyl group, or a haloethyl group; and X is C.sub.1 -C.sub.4 alkoxy group, a C.sub.2 -C.sub.6 alkenyloxy group, a C.sub.2 -C.sub.6 alkoxyalkoxy group, a C.sub.3 -C.sub.8 alkynyloxy group, a hydroxy group, a halomethyloxy group, a 3-chloro-2-propenoxy group, a 1-ethynyl-1-cyclohexyloxy group, or a haloethyloxy group.

### Claim 12 (depends on 11)

A herbidical composition of claim 11, wherein R.sup.2 is a halomethyl group.

### Claim 13 (depends on 12)

A herbidical composition of claim 12, wherein the halomethyl group is a difluoromethyl group.

### Claim 14 (depends on 11)

A herbicidal composition of claim 11, wherein X is a C.sub.1 -C.sub.4 alkoxy group, a C.sub.2 -C.sub.6 alkenyloxy group, a C.sub.2 -C.sub.6 alkoxyalkoxy group, a 3-chloro-2-propenoxy group, a 1-ethynyl-1-cyclohexyloxy group, or a C.sub.3 -C.sub.8 alkynyloxy group.

### Claim 15 (depends on 11)

A herbicidal composition of claim 11, wherein R.sup.2 is a halomethyl group; and X is a C.sub.1 -C.sub.4 alkoxy group, a C.sub.2 -C.sub.6 alkenyloxy group, a C.sub.2 -C.sub.6 alkoxyalkoxy group, a 3-chloro-2-propenoxy group, a 1-ethynyl-1-cyclohexyloxy group, or a C.sub.3 -C.sub.8 alkynyloxy group.

### Claim 16 (depends on 15)

A herbicidal composition of claim 15, wherein the halomethyl group is a difluoromethyl group.

### Claim 17 (depends on 11)

A herbicidal composition of claim 11, wherein the .DELTA..sup.2 -1,2,4-triazolin-5-one derivative is 1-(2,4-dichloro-5-isopropoxyphenyl)-3-methyl-4-difluromethyl-.DELTA..sup.2 -1,2,4-triazolin-5-one.

### Claim 18 (depends on 11)

A herbicidal composition of claim 11, wherein the .DELTA..sup.2 -1,2,4-triazolin-5-one derivative is 1-(2,4-dichloro-5-allyloxyphenyl)-3-methyl-4-difluoromethyl-.DELTA..sup.2 -1,2,4-triazolin-5-one.

### Claim 19 (depends on 11)

A herbicidal composition of claim 11, wherein the .DELTA..sup.2 -1,2,4-triazolin-5-one derivative is 1-(2,4-dichloro-5-propargyloxyphenyl)-3-methyl-4-difluoromethyl-.DELTA..su p.2 -1,2,4-triazolin-5-one.

### Claim 20 (depends on 11)

A herbicidal composition of claim 11, wherein the .DELTA..sup.2 -1,2,4-triazolin-5-one derivative is 1-(2,4-dichloro-5-methoxymethoxyphenyl)-3-methyl-4-difluromethyl-.DELTA..s up.2 -1,2,4-triazolin-5-one.

### Claim 21 (depends on 1)

A method of killing plants comprising applying to the plants a herbicidally effective amount of a compound according to claim 1.

### Claim 22 (depends on 2)

A method of killing plants comprising applying to the plants a herbicidally effective amount of a compound according to claim 2.

### Claim 23 (depends on 3)

A method of killing plants comprising applying to the plants a herbicidally effective amount of a compound according to claim 3.

### Claim 24 (depends on 4)

A method of killing plants comprising applying to the plants a herbicidally effective amount of a compound according to claim 4.

### Claim 25 (depends on 5)

A method of killing plants comprising applying to the plants a herbicidally effective amount of a compound according to claim 5.

### Claim 26 (depends on 6)

A method of killing plants comprising applying to the plants a herbicidally effective amount of the compound of claim 6.

### Claim 27 (depends on 7)

A method of killing plants comprising applying to the plants a herbicidally effective amount of the compound of claim 7.

### Claim 28 (depends on 8)

A method of killing plants comprising applying to the plants a herbicidally effective amount of the compound of claim 8.

### Claim 29 (depends on 9)

A method of killing plants comprising applying to the plants a herbicidally effective amount of the compound of claim 9.

### Claim 30 (depends on 10)

A method of killing plants comprising applying to the plants a herbicidally effective amount of the compound of claim 10.

### Claim 31 (depends on 21)

A method according to claim 21 wherein the compound is applied before emergence of the plants.

### Claim 32 (depends on 21)

A method according to claim 21 wherein the compound is applied after emergence of the plants.

### Claim 33 (depends on 1)

A method of selectively killing weeds in a crop of useful plants comprising applying to the crop an amount of a compound of claim 1 effective to kill the weeds but insufficient to kill the useful crop.

### Claim 34 (depends on 33)

A method according to claim 33 wherein the herbicide is applied efore emergence of the plants.

### Claim 35 (depends on 34)

A method according to claim 34 wherein the crop is rice.

### Claim 36 (depends on 33)

A method according to claim 33 wherein the herbicide is applied after emergence of the plants.

### Claim 37 (depends on 36)

A method according to claim 36 wherein the crop is rice or soybeans.

### Claim 38 (depends on 5)

A compound according to claim 5 wherein X is 1-ethynyl-1-cyclohexyloxy.